A Travel Price Comparison for United States of America Key West vs. Hilton Head Island for Families, Resorts, Beaches, and Couples

Should you visit Key West or Hilton Head Island?

Which is cheaper to visit? Which is more expensive for vacation?

Should I visit Key West or Hilton Head Island? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.

Key West

Key West is a laid-back, quirky, and eclectic town. This is a charming small with plenty of activities, too. With stunning beauty, it attracts visitors from all around. Because of its quaint atmosphere, it draws plenty of visitors, too. It's also popular because of the food, scuba diving and snorkeling, and beaches.

Hilton Head Island

Hilton Head Island is a relaxing, peaceful, and beautiful coastal town. It's a beautiful place to visit, too. And you can't forget about the beaches, shopping, and food.

Key West and Hilton Head Island: Pros and Cons

Is there more to do in Key West or Hilton Head Island?

Tourists will generally find more to do in Key West. Although Key West and Hilton Head Island are both popular with visitors, Key West has more sights, activities, and attractions for travelers. Key West is more popular for its nightlife, scuba diving & snorkeling, historical sights, small town charm, impressive beauty, and quaint atmosphere, while Hilton Head Island is known for its shopping. Key West is more touristy than Hilton Head Island and is popular for its festive nightlife, quirky town center, colorful personality, adrenaline-filled watersports, stunning beaches, turquoise water, and location at the southernmost point of the continental U.S. It is also home to Duval Street. Hilton Head Island is popular for its long sandy beaches, many golf courses, popular tennis camps, and accessible bike trails.

How is Key West different from Hilton Head Island?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Hilton Head Island and Key West. Then, you can decide for yourself which place is better for your next trip.

Is the Food Better in Key West or Hilton Head Island? Which Destination has the Best Restaurants?

There are opportunities to sample the local cuisine at good restaurants in both Key West and Hilton Head Island.

Visitors will find a budding food and restaurant scene in Key West. Head to town for local restaurants with quirky atmospheres. There are many local dishes to sample, be the town is most known for its stone crabs, conch fritters, and Mahi Mahi sandwiches. You'll also find cold drinks and waterfront dining areas.

Hilton Head Island is becoming an appealing option for foodies. The island has many famous restaurants but reservations during the summer are a must. Restaurants can get very crowded during peak times. For some of the best restaurants head to Shelter Cove or Harbour Town. Popular local dishes include fried seafood and oysters.

Is Key West or Hilton Head Island Better for Nightlife?

Key West is a very popular place for its evening party scene. However, Hilton Head Island is lacking in good options for nightlife.

Key West has a large number of nightlife venues. This area has some of the most lively nightlife in the Florida Keys. There are quirky bars and fun hangouts where you can spend the evening. The party starts at Mallory Square around sunset and many bars stay open well into the early hours. You can also enjoy sunset cruises or pass your time at one of the many tiki bars.

Things get quiet in the evenings in Hilton Head Island. There are a few sports bars and comedy clubs, but nightlife isn't really a thing in Hilton Head. This is very much a family destination that shuts down with the sunset.

Is Key West or Hilton Head Island Better for Resorts?

Key West and Hilton Head Island offer a relatively similar set of great luxury resort options.

Key West is known as a popular and fun resort destination. There are a number of high end resorts around the island, many with recognizable names such as the Hyatt and Hilton. Prices can be high, but these resorts often come with reliable luxury.

Vacationers can choose from a number of terrific resorts in Hilton Head Island. Most of the accommodation in the area is in the form of weekly condo rentals, which usually include a pool and outdoor space. Tennis and golf are also popular on the island so many resorts have facilities for each.

Is Key West or Hilton Head Island Better for Scuba Diving and Snorkeling?

Key West is very good for snorkeling and scuba diving. However, Hilton Head Island is not a scuba or snorkeling destination.

It's worth going snorkeling or scuba diving in Key West. There are a number of dive shops and snorkeling excursions that leave from Key West. Like many tourist areas these days, the coral shows its damage from the crowds, but you'll likely see some barracuda or a Grouper.

Hilton Head Island is not a scuba or snorkeling destination.

Is Key West or Hilton Head Island Better for Beaches?

For a relaxing beach holiday, both Key West and Hilton Head Island are great choices.

Key West is considered a top beach destination. One of the best beaches in the area is Fort Zachary Taylor Historic State Park. The beach has soft sand and stunning turquoise water. As is typical in the Keys, the water stays shallow for great distances.

Hilton Head Island is a very popular place to visit for its beaches. The island has nice beaches that are popular with families. They are great for swimming during the spring, summer, and fall seasons. While some beaches may get a bit crowded during peak holidays, they're usually pretty relaxed and less crowded than many nearby beaches.

Is Key West or Hilton Head Island Better for its Old Town?

Key West is a very popular place for its historic old town charm. However, Hilton Head Island does not have a historic old town.

There is a nice variety of sights in the old town of Key West. The town has the most charming Old Town areas in the Florida Keys. Head to Mallory Square for the sunset street performers and explore the historic streets around Duval Street.

Hilton Head Island does not have a historic old town.

Is the Shopping Better in Key West or Hilton Head Island?

Hilton Head Island is a popular place for its shopping opportunities. However, Key West is a mediocre town for its shopping areas.

Hilton Head Island offers some nice shopping areas. The area has upscale shopping with designer names and local venues. Popular shopping areas include Shelter Cove Town Center and Harbor Town.

Key West has some good spots for those that want to go shopping. While it definitely has its share of gimmicky souvenir shops and t-shirt stores, there are still a number of art galleries and local shops around Key West where you can enjoy shopping.

Is Key West or Hilton Head Island Better for Families?

Hilton Head Island is renowned for its family-friendly activities. Also, Key West is not as famous, but is still a good town to visit for its kid-friendly activities.

As it has a large number of activities for kids, Hilton Head Island is a very family-friendly destination. This area is a popular family-friendly beach destination with a number of summer events for the whole family, peaceful beaches, and family-friendly restaurants throughout. Older kids will enjoy cycling around the island's many bike trails or attending a popular tennis camp.

You'll find plenty of family-friendly things to do in Key West. Families that enjoy snorkeling, aquariums, water sports, and exploring new places will enjoy visiting this part of the Florida Keys. There are many ways to get out on the water from kayaking and snorkeling to glass bottom boat tours and sunset cruises. There are also many kid-friendly beaches in the area. The town can have a party atmosphere, but it's not hard to find a more family-friendly area where everyone can have fun.

Is Key West or Hilton Head Island Better for Couples?

Key West is a very popular place for couples. Also, Hilton Head Island is not quite as popular, but is fairly good for romance.

Key West makes for a fun place to visit for a couple. From Mallory Square to the beautiful nearby parks, Key West makes a wonderful, romantic destination. Whether it's your honeymoon, an anniversary, or simply a couples' retreat, Key West is a great option. You can sip wine on a sunset cruise or dine at one of the many character-filled restaurants in town. If you are looking for a party, it's not hard to find, but if you want a more laid back holiday, that's also possible.

Hilton Head Island is a nice destination for couples. While the area is most popular with families, it is a fun place to explore as a couple because of the many high end restaurants and the beautiful setting. Couples can rent bikes to explore or play a friendly game of tennis.

Is Key West or Hilton Head Island Better for Students?

Key West is a very popular place for its student-friendly activities. However, Hilton Head Island is not popular with students.

Key West is very popular with students. It's a great spring break destination with a quirky personality and many great activities.

Hilton Head Island is not popular with students.

Is Key West or Hilton Head Island Better for Public Transit? Which Is Easier to Get Around Without a Car?

Neither Key West or Hilton Head Island offer decent public transit.

Public transit is limited or non-existant in Key West. Public transportation in Key West is limited to a few buses.

Public transit is quite limited in Hilton Head Island. You must have a car to get most places on the island, unless you bike. Rush hour during summer months can have intense traffic.

Is Key West or Hilton Head Island a more walkable city?

Key West is very good for its ease of walking around. However, Hilton Head Island is lacking in good options for its walkability.

Key West is a somewhat walkable town. The town is the most walkable part of the Florida Keys. The area around Mallory Square and Duval Street is the most pedestrian friendly.

Hilton Head Island is generally not very walkable. You really need a car to get around, but for those who are motivated, there is a great network of bike trails. It's mostly used for recreational purposes though.

For even more information, also check out Is Key West Worth Visiting? and Is Hilton Head Island Worth Visiting?.

Should I spend more time in Hilton Head Island or Key West?

How long in Key West or Hilton Head Island?

Both Key West and Hilton Head Island have a number of activities to choose from. In our opinion, Key West has more to see and do, so we recommend that you spend more time in Key West than Hilton Head Island. However, 5-7 days is a good amount of time to spend in either destination.

Families should spend more time in Hilton Head Island than Key West. Because of the many family-friendly attractions and fun things to do for kids in Hilton Head Island, it's a great place to visit with the whole family.

Couples should spend more time in Key West than Hilton Head Island. You'll find plenty of romantic sights and fun activities in Key West that are great for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Key West than Hilton Head Island if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Key West.

One day in Key West or Hilton Head Island?

Visitors enjoy the food and scuba diving and snorkeling when visiting the laid-back destination of Key West. This town offers something for everyone. Exploring the old town is a popular activity. But since there are so many activities, you'll likely want to spend more than one day exploring.

The coastal town of Hilton Head Island offers shopping and food. Most people come for the beaches. With so much to do, one day is probably not enough time to see everything. It will give you the chance to have new experiences.

A weekend in Key West or Hilton Head Island?

Key West is a popular place to visit. Visitors enjoy the scuba diving and snorkeling and nightlife when visiting the bustling town of Key West. People enjoy relaxing at one of the resorts. With so much to do, a weekend is probably not enough time to see everything.

Hilton Head Island is a popular place that is full of things to see and experience. People enjoy relaxing at one of the resorts. But since there are so many activities, you'll likely want to spend more than a weekend exploring. Take your pick from the many activities offered here.

Five days in Key West or Hilton Head Island?

Visitors enjoy the nightlife and food when visiting the quaint destination of Key West. This is a popular place to visit for five days. Most visitors spend time around the old town while in the area. Anyone can find something fun to do here. Five days is a great amount of time to relax and see the many things that Key West has to offer.

Hilton Head Island is a popular choice for travelers. Five days here is typical. While some people choose to spend more or less time in Hilton Head Island, five days is sufficent for most. The entire region has so many activities, and you'll want time to do everything.

A week in Key West or Hilton Head Island?

Key West is a popular place that is full of things to see and experience. If you have one week, this town makes for a great vacation. Visiting the old town is also a must. It offers something for everyone. With all of its activities, you can easily fill one week here.

Hilton Head Island is a great place to explore. It is common to spend one week here. It's also a great beach destination, too. One week is a great amount of time to relax and see the many things that Hilton Head Island has to offer. This coastal town offers something for everyone.

For some great organized tour ideas, see The Best One-Week (7-Day) Tours from Los Angeles, The Best One-Week (7-Day) Tours from New York City, The Best 2-Week Tours from New York City, and The Best 2-Week Tours from Anchorage.

When we compare the travel costs of actual travelers between Key West and Hilton Head Island, we can see that Key West is more expensive. And not only is Hilton Head Island much less expensive, but it is actually a significantly cheaper destination. So, traveling to Hilton Head Island would let you spend less money overall. Or, you could decide to spend more money in Hilton Head Island and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Key West would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Key West than you might in Hilton Head Island.

If you're trying to decide if either of these two destinations are within your price range, also see Is Key West Expensive? and Is Hilton Head Island Expensive?.

Which is Bigger, Key West or Hilton Head Island?

Hilton Head Island has a larger population, and is about 40% larger than the population of Key West. When comparing the sizes of Key West and Hilton Head Island, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.

When is the best time to visit Key West or Hilton Head Island?

Both places have a temperate climate with four distinct seasons. As both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Key West or Hilton Head Island in the Summer?

Both Hilton Head Island and Key West during the summer are popular places to visit. The beaches, snorkeling, the small town charm, and the family-friendly experiences are the main draw to Key West this time of year. Furthermore, many travelers come to Hilton Head Island for the beaches and the family-friendly experiences.

In the summer, Key West is around the same temperature as Hilton Head Island. Typically, the summer temperatures in Key West in July average around 84°F (29°C), and Hilton Head Island averages at about 82°F (28°C).

In Hilton Head Island, it's very sunny this time of the year. It's quite sunny in Key West. In the summer, Key West often gets more sunshine than Hilton Head Island. Key West gets 328 hours of sunny skies this time of year, while Hilton Head Island receives 267 hours of full sun.

Hilton Head Island gets a good bit of rain this time of year. Key West usually gets less rain in July than Hilton Head Island. Key West gets 3.3 inches (83 mm) of rain, while Hilton Head Island receives 7.9 inches (200 mm) of rain this time of the year.

Should I visit Key West or Hilton Head Island in the Autumn?

The autumn attracts plenty of travelers to both Key West and Hilton Head Island. Many travelers come to Key West for the shopping scene, the small town atmosphere, and the natural beauty of the area. Furthermore, many visitors come to Hilton Head Island in the autumn for the shopping scene and the natural beauty of the area.

In October, Key West is generally a little warmer than Hilton Head Island. Daily temperatures in Key West average around 80°F (27°C), and Hilton Head Island fluctuates around 68°F (20°C).

People are often attracted to the plentiful sunshine in Hilton Head Island this time of the year. In Key West, it's very sunny this time of the year. Key West usually receives more sunshine than Hilton Head Island during autumn. Key West gets 258 hours of sunny skies, while Hilton Head Island receives 223 hours of full sun in the autumn.

Key West gets a good bit of rain this time of year. In October, Key West usually receives more rain than Hilton Head Island. Key West gets 5.1 inches (129 mm) of rain, while Hilton Head Island receives 2.8 inches (71 mm) of rain each month for the autumn. June to November is the hurricane season in Key West.

Should I visit Key West or Hilton Head Island in the Winter?

The winter brings many poeple to Key West as well as Hilton Head Island. Many visitors come to Key West in the winter for the shopping scene and the cuisine. Additionally, most visitors come to Hilton Head Island for the shopping scene and the cuisine during these months.

Key West is much warmer than Hilton Head Island in the winter. The daily temperature in Key West averages around 70°F (21°C) in January, and Hilton Head Island fluctuates around 48°F (9°C).

People are often attracted to the plentiful sunshine in Key West this time of the year. In the winter, Key West often gets more sunshine than Hilton Head Island. Key West gets 252 hours of sunny skies this time of year, while Hilton Head Island receives 176 hours of full sun.

Key West usually gets less rain in January than Hilton Head Island. Key West gets 1.7 inches (43 mm) of rain, while Hilton Head Island receives 2.9 inches (74 mm) of rain this time of the year.

Should I visit Key West or Hilton Head Island in the Spring?

Both Hilton Head Island and Key West are popular destinations to visit in the spring with plenty of activities. Most visitors come to Key West for the beaches, the small town charm, and the natural beauty during these months. Also, the spring months attract visitors to Hilton Head Island because of the beaches and the natural beauty.

In the spring, Key West is a little warmer than Hilton Head Island. Typically, the spring temperatures in Key West in April average around 77°F (25°C), and Hilton Head Island averages at about 67°F (19°C).

It's quite sunny in Hilton Head Island. The sun comes out a lot this time of the year in Key West. Key West usually receives more sunshine than Hilton Head Island during spring. Key West gets 326 hours of sunny skies, while Hilton Head Island receives 275 hours of full sun in the spring.

In April, Key West usually receives less rain than Hilton Head Island. Key West gets 0.8 inches (21 mm) of rain, while Hilton Head Island receives 2.9 inches (74 mm) of rain each month for the spring. June to November in Key West is the hurricane season.

Typical Weather for Hilton Head Island and Key West